Methanol → HCID 57860070, compound

HRID 1947161Notes

Reaction equation

HRID 1947161 reaction equation
C([O:4][CH2:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[N:29]([CH3:30])[C:28]3[C:27]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[N:21]([CH2:31][C:32]4[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=4)[C:20](=[O:39])[C:19]=3[C:18]=2[O:40][CH3:41])=[O:16])[CH2:10][CH2:9]1)=[O:7])(=O)C.C(=O)([O-])[O-].[K+].[K+].CO.O>C1COCC1.C(=O)([O-])O.[Na+]>[Cl:38][C:35]1[CH:34]=[CH:33][C:32]([CH2:31][N:21]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=3[C:28]3[N:29]([CH3:30])[C:17]([C:15]([NH:14][CH:11]4[CH2:10][CH2:9][N:8]([C:6](=[O:7])[CH2:5][OH:4])[CH2:13][CH2:12]4)=[O:16])=[C:18]([O:40][CH3:41])[C:19]=3[C:20]2=[O:39])=[CH:37][CH:36]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 11430Potassium CarbonateHCID 66892528HCID 66892528, compound

Product 1

HCID 57860070HCID 57860070, compoundYield 12.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 2-[4-({[5-(4-chlorobenzyl)-3-methoxy-1-methyl-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]quinolin-2-yl]carbonyl}amino)piperidin-1-yl]-2-oxoethyl acetate (60 mg) and potassium carbonate (72 mg, 0.52 mmol) in THF (2 mL)-methanol (1 mL)-water (1 mL) was stirred at room temperature for 3 hr. The reaction mixture was diluted with saturated sodium hydrogen carbonate solution, and extracted twice with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give the title compound (7 mg, 2%) as white crystals.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-f9b00d2508ac4f8f97a681479cdc2cc8
Source dataset
uspto-grants-2013_03
Patent number
US08399449B2

Reaction notes

Loading…